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He pleaded guilty in a sensational Toronto terrorism trial, served his time and then left Canada to fight in Syria where he was reportedly killed.

Ali Mohamed Dirie was convicted for his involvement in the 2006 terrorism plot to blow up Toronto and area targets, in a case that was dubbed the “Toronto 18” because of the number of youths and Muslim men arrested.

After his release in 2011, Dirie reportedly left Canada for Syria.

He is one of dozens of Canadians who have joined the conflict in Syria where more than 100,000 have died, as rebel fighters and Al Qaeda militants battle loyalists of President Bashar Assad’s regime.

Security sources estimate that at least 100 Canadians — mainly in their 20s and from Ontario and Alberta — have left for Syria in the last year. Dirie is not the first to be killed.

“I (still) oppose it and I think it’s an unjust war,” Dirie said at his parole hearing in 2010 when asked about Canada’s involvement in the war in Afghanistan. “But I don’t think I live in a tyrannical country where I’m not allowed to hold those opinions.”

Members of the Toronto 18 had cited Afghanistan as one of their motivations for plots to attack targets, which included Ottawa’s Parliament buildings and the Toronto office of Canada’s spy service.

“At the end of the day, what I’m trying to say is that I’ll be out in a year,” Dirie said according to a Canadian Press report of the parole hearing. “I don’t have to prove anything to anybody here, I’ll have to prove myself to the public and that’s all that matters in the end.”

The National Parole Board denied Dirie parole, ruling he showed a persistent pattern of violent behaviour and remained likely to harm others.

Mubin Shaikh, who worked undercover for the RCMP to infiltrate the group, told the Star that Dirie’s death had been rumoured for weeks.

“Terrorist convicts are not ordinary prisoners. Some charismatic individuals may use their time behind bars to promote their extremist views, prosthelytizing radical ideologies in an attempt to attract and recruit members of the general prison population,” they said, arguing recruitment attempts must be proactively disrupted.

A former imam who worked with Toronto 18 inmates said his contract expired in March due to a controversial decision last fall to eliminate part-time prison chaplains.

Saad Khalid, who was convicted along with Dirie but is serving a 20-year sentence, was reportedly devastated by the imam’s departure.

“He broke down and cried,” Imam Ramzy Ajem told the Star. “He was holding on to me and didn’t want to let me go.”

Mubin said Canada lags behind other Western countries in terms of prison counseling. “They go in there and they fester,” he said. “You don’t get better by sitting in a prison cell.”

Couple this with the lure of the jihad Syria — heightened especially with the lack of international involvement and daily horrific images of the slaughter by Assad’s regime — and Shaikh said the circumstances of Dirie’s death shouldn’t come as a surprise.

Robert Nuttall, Dirie’s lawyer during the Toronto 18 trial, said he was saddened and surprised to hear about his former client’s death.

Nuttall, reached by phone Wednesday, said he had not been in contact with the Dirie family for years.

Dirie was born in Somalia on Aug. 10, 1983, coming over to Canada when he was 7.

In a 2003 Star piece on a woodworking employment program, a 19-year-old Dirie is featured learning carpentry skills.

The young Dirie said he had his eye on a college program to become an X-ray technician, with his paycheques going toward savings and rent.

“Life was very stressful for me – just thinking about how to pay the bills,” he told the Star about struggling to find a job.

“I was totally lost. Now, I’m on the right track.”

Dirie was arrested in 2005 at the U.S. border trying to re-enter Canada with two loaded handguns taped to his thighs. He pleaded guilty to importing and possession of firearms and ammunition and was sentenced to two years.

In prison, he conspired on how to obtain weapons for members of the Toronto 18 plot, even receiving a package of books and CDs dubbed a “Qur’an kit.”

It contained hidden violent videos of attacks and bombings of military personnel. One, titled “Return of the Crusaders,” featured scenes of injured women and children in Iraq and mosque bombings. It included a clip of Osama bin Laden calling for terrorist attacks.

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